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It's really about balancing Italy and not exacerbating his main quirks and personality traits. A lot of players seem to get the balance wrong when it comes to playing him. Some make him just cry out for Germany all the time and others make him a hyper, over the top moe blob. Italy is a very cute character, but it's not always in the most conventional ways (usually it's Spain, France, Rome, or Prussia find his failings endearing and adorable). While he's not the deepest thinker, he feels things deeply. That doesn't make him an emotional wreck or anything, but he has a lot more depth to him versus what most people perceive. I wouldn't say he was a deep character in general, but he's actually deep compared to most Hetalia characters as he's fleshed out a lot more. Italy has subtle character depth that takes looking at the series at a whole rather than just one episode at a time.

Common mistakes I see is the fact asking for Germany to save him too much. It's in certain situations where he 1) extremely dangerous and he freaks out 2) really small things like tying his shoes 3) Wants to get out of something and knows Germany can do it better than him. He rather run away for the most part, but if there is a woman around, he'll try to step up his game (probably failing, though). I also like to note Italy and Germany are still friends in the series and he's still friends with Japan. Germany and Italy have traveled to Taiwan and Turkey set in the modern day strips. Wikipedia's international relations shouldn't be your go to source to figure out Italy's closest friends.

Italy lives in his own world sometimes because he likes nice, pretty things and having fun. He's easily distracted by things he likes and goes at his own pace. When he needs to step his game up, he will if he has to. Most of the time he feels someone else will do it for him, especially Germany or another ally during their various war strips (WWII, WWI, various battle). I also see sometimes Italy being super affectionate to Romano but Romano being the only asshole. Italy has issues with his brother, and he's not 100% guilt free as while he is affectionate, he openly admits Romano is a dick. That doesn't mean Italy hates him, but they're not the most compatible, but Italy does try at least.

Definitely agreeing with everything you said here.

I think people sometimes forget about the strips about how cunning and tough young Italy could be. Even Germany was surprised when Turkey told him about Italy beating him up in the past when he was a kid because it's not what anyone expects of him now. Italy had the stores to be a stronger, tougher characters but he's also lazy and has no problem not doing things if he thinks someone else will do it for him. Growing up with someone like Austria probably didn't help since we all know how much Austria sucked at war and standing up for himself most of the time. And the fact he thought Veneziano was a girl for centuries. Italy's upbringing was not the easiest.

Also we see time and time again how much Italy does want to be seen as useful. He's just not that good at the things he does to try and prove it. Food? Italy is known to be a great cook and so he doesn't feel the need to prove himself there. In the military? He made a gun and focused on making it easier to clean instead of making it a more effective weapon. The things he thinks are important are not the things everyone else might prioritize. Where Japan focused on safe cars, Italy focused on fast cars that would make the owner look good. It doesn't make him stupid, because plenty of people prefer those cars to Japan's safe ones. It's just his different priorities and outlook on life.

He's even one of the few people who recognizes Canada on sight when England can't do it and they aren't even that closely connected. That shows how much of a people person Italy is and how he picks up on things that a lot of people ignore. They don't see it as important but he does.

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